CA2195640C - Oxidase-promoted gelling of phenolic polymers - Google Patents
Oxidase-promoted gelling of phenolic polymers Download PDFInfo
- Publication number
- CA2195640C CA2195640C CA002195640A CA2195640A CA2195640C CA 2195640 C CA2195640 C CA 2195640C CA 002195640 A CA002195640 A CA 002195640A CA 2195640 A CA2195640 A CA 2195640A CA 2195640 C CA2195640 C CA 2195640C
- Authority
- CA
- Canada
- Prior art keywords
- phenolic
- laccase
- substituents
- arabinoxylan
- pectic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 229920000642 polymer Polymers 0.000 title description 16
- 238000000034 method Methods 0.000 claims abstract description 45
- 239000000463 material Substances 0.000 claims abstract description 32
- 108010029541 Laccase Proteins 0.000 claims abstract description 29
- 125000001424 substituent group Chemical group 0.000 claims abstract description 12
- 239000012736 aqueous medium Substances 0.000 claims abstract description 8
- 229920001277 pectin Polymers 0.000 claims description 41
- 239000001814 pectin Substances 0.000 claims description 31
- 235000010987 pectin Nutrition 0.000 claims description 30
- 239000005017 polysaccharide Substances 0.000 claims description 26
- 229920001282 polysaccharide Polymers 0.000 claims description 21
- 229920000617 arabinoxylan Polymers 0.000 claims description 14
- 235000016068 Berberis vulgaris Nutrition 0.000 claims description 10
- 241000335053 Beta vulgaris Species 0.000 claims description 10
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 claims description 10
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- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 10
- 235000013985 cinnamic acid Nutrition 0.000 claims description 9
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 9
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 8
- 229930016911 cinnamic acid Natural products 0.000 claims description 8
- 150000004676 glycans Chemical class 0.000 claims description 8
- UGXQOOQUZRUVSS-ZZXKWVIFSA-N [5-[3,5-dihydroxy-2-(1,3,4-trihydroxy-5-oxopentan-2-yl)oxyoxan-4-yl]oxy-3,4-dihydroxyoxolan-2-yl]methyl (e)-3-(4-hydroxyphenyl)prop-2-enoate Chemical compound OC1C(OC(CO)C(O)C(O)C=O)OCC(O)C1OC1C(O)C(O)C(COC(=O)\C=C\C=2C=CC(O)=CC=2)O1 UGXQOOQUZRUVSS-ZZXKWVIFSA-N 0.000 claims description 7
- 235000013339 cereals Nutrition 0.000 claims description 6
- 125000000089 arabinosyl group Chemical group C1([C@@H](O)[C@H](O)[C@H](O)CO1)* 0.000 claims description 5
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- -1 phenolic polysaccharides Chemical class 0.000 description 15
- 150000004804 polysaccharides Chemical class 0.000 description 15
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- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 description 6
- 235000001785 ferulic acid Nutrition 0.000 description 6
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- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 description 6
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 6
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- 150000004783 arabinoxylans Chemical class 0.000 description 5
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 5
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- 238000002360 preparation method Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 4
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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- 102000003992 Peroxidases Human genes 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 108010041969 feruloyl esterase Proteins 0.000 description 3
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- SATHPVQTSSUFFW-UHFFFAOYSA-N 4-[6-[(3,5-dihydroxy-4-methoxyoxan-2-yl)oxymethyl]-3,5-dihydroxy-4-methoxyoxan-2-yl]oxy-2-(hydroxymethyl)-6-methyloxane-3,5-diol Chemical compound OC1C(OC)C(O)COC1OCC1C(O)C(OC)C(O)C(OC2C(C(CO)OC(C)C2O)O)O1 SATHPVQTSSUFFW-UHFFFAOYSA-N 0.000 description 2
- 229920000189 Arabinogalactan Polymers 0.000 description 2
- 239000001904 Arabinogalactan Substances 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 108010031396 Catechol oxidase Proteins 0.000 description 2
- 102000030523 Catechol oxidase Human genes 0.000 description 2
- AEMOLEFTQBMNLQ-YMDCURPLSA-N D-galactopyranuronic acid Chemical group OC1O[C@H](C(O)=O)[C@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-YMDCURPLSA-N 0.000 description 2
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 101710121765 Endo-1,4-beta-xylanase Proteins 0.000 description 2
- SHZGCJCMOBCMKK-JFNONXLTSA-N L-rhamnopyranose Chemical compound C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O SHZGCJCMOBCMKK-JFNONXLTSA-N 0.000 description 2
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 description 2
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- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 235000019312 arabinogalactan Nutrition 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
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- LZFOPEXOUVTGJS-ONEGZZNKSA-N trans-sinapyl alcohol Chemical compound COC1=CC(\C=C\CO)=CC(OC)=C1O LZFOPEXOUVTGJS-ONEGZZNKSA-N 0.000 description 2
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0045—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Galacturonans, e.g. methyl ester of (alpha-1,4)-linked D-galacturonic acid units, i.e. pectin, or hydrolysis product of methyl ester of alpha-1,4-linked D-galacturonic acid units, i.e. pectinic acid; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0057—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Xylans, i.e. xylosaccharide, e.g. arabinoxylan, arabinofuronan, pentosans; (beta-1,3)(beta-1,4)-D-Xylans, e.g. rhodymenans; Hemicellulose; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
- C08L5/06—Pectin; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/04—Polysaccharides, i.e. compounds containing more than five saccharide radicals attached to each other by glycosidic bonds
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Molecular Biology (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- General Chemical & Material Sciences (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Jellies, Jams, And Syrups (AREA)
- Cosmetics (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Enzymes And Modification Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK0882/94 | 1994-07-26 | ||
| DK88294 | 1994-07-26 | ||
| PCT/DK1995/000317 WO1996003440A1 (en) | 1994-07-26 | 1995-07-26 | Oxidase-promoted gelling of phenolic polymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2195640A1 CA2195640A1 (en) | 1996-02-08 |
| CA2195640C true CA2195640C (en) | 2007-06-12 |
Family
ID=8098589
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002195640A Expired - Fee Related CA2195640C (en) | 1994-07-26 | 1995-07-26 | Oxidase-promoted gelling of phenolic polymers |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6232101B1 (hu) |
| EP (1) | EP0750641B1 (hu) |
| JP (1) | JPH10502962A (hu) |
| AT (1) | ATE198604T1 (hu) |
| AU (1) | AU3074595A (hu) |
| BR (1) | BR9508350A (hu) |
| CA (1) | CA2195640C (hu) |
| CZ (1) | CZ287861B6 (hu) |
| DE (1) | DE69519852T2 (hu) |
| ES (1) | ES2155523T3 (hu) |
| FI (1) | FI114987B (hu) |
| HU (1) | HU220197B (hu) |
| PT (1) | PT750641E (hu) |
| WO (1) | WO1996003440A1 (hu) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9508350A (pt) | 1994-07-26 | 1997-11-04 | Novo Nordisk As | Processo para provocar a gelificação ou o aumento de viscosidade de um meio aquoso contento material polimérico propenso a gelificação produto geleficado produto de gel desidratado ou seco e uso dos produtos |
| ATE201699T1 (de) * | 1996-01-26 | 2001-06-15 | Novozymes As | Enzymatische gelierung von polymermaterialien |
| EA199900475A1 (ru) * | 1996-11-21 | 1999-12-29 | Е.И. Дюпон Де Немур Энд Компани | Получение растительных гелей |
| AU747863B2 (en) | 1997-03-20 | 2002-05-23 | Cambridge Biopolymers Limited | Improvements relating to bran gels |
| GB9718518D0 (en) * | 1997-09-01 | 1997-11-05 | Dalgety Plc | Fractionation of Hemicellulosic Materials |
| WO1999032652A1 (en) * | 1997-12-19 | 1999-07-01 | Novo Nordisk A/S | Modification of polysaccharides by means of a phenol oxidizing enzyme |
| GB9815200D0 (en) * | 1998-07-14 | 1998-09-09 | Du Pont Uk | Extraction of hemicellulosic materials |
| GB9900227D0 (en) * | 1999-01-06 | 1999-02-24 | Danisco | Use of a composition |
| GB9904939D0 (en) * | 1999-03-05 | 1999-04-28 | Du Pont Uk | Polymer compositions |
| JP4135502B2 (ja) | 2001-01-31 | 2008-08-20 | 生化学工業株式会社 | 架橋多糖スポンジ |
| DE60211864T2 (de) * | 2001-02-26 | 2006-11-30 | Unilever N.V. | Verfahren zur herstellung eines geschäumten produkts auf basis von oxydierten ferulasäurekomponenten |
| US7015022B2 (en) * | 2002-06-07 | 2006-03-21 | University Of Medicine & Dentistry Of New Jersey | Mammalian catalase-dependent oxidation processes and methods for stimulating oxidative activities |
| AU2003236713A1 (en) * | 2002-06-24 | 2004-01-06 | Unilever Plc | Stable oil in water emulsion |
| BR0313422A (pt) * | 2002-08-19 | 2005-06-28 | Unilever Nv | Método para a preparação de um confeito congelado areado, composição base para um confeito areado congelado, confeito areado congelado e lata de aerossol |
| DE10244124A1 (de) * | 2002-09-23 | 2004-04-01 | Satia Gmbh | Wasserhaltiges Medium mit erhöhter Viskosität, Verfahren zur Herstellung und Verwendung |
| AU2003289862A1 (en) * | 2002-12-19 | 2004-07-14 | Unilever Plc | Polymer composition suitable for use in food products |
| CA2535526C (en) | 2003-08-11 | 2015-09-29 | Diversa Corporation | Laccases, nucleic acids encoding them and methods for making and using them |
| US20060128939A1 (en) * | 2004-12-03 | 2006-06-15 | Vijayendra Kumar | One pot process for making polymeric antioxidants |
| CN101087535A (zh) * | 2004-12-23 | 2007-12-12 | 荷兰联合利华有限公司 | 冷冻或冷藏的蔬菜制品 |
| CN103270052B (zh) * | 2010-11-23 | 2017-09-19 | 艾克海丽克斯有限责任公司 | 一种增加包含芳族部分的木质甘露聚糖和木聚糖的分子量的方法 |
| WO2014083032A1 (en) | 2012-11-28 | 2014-06-05 | Pectcof B.V. | Pectin extraction from coffee pulp |
| WO2014147053A1 (en) * | 2013-03-19 | 2014-09-25 | Nestec S.A. | Plant based emulsifier for frozen confection products |
| FR3011841B1 (fr) * | 2013-10-14 | 2016-09-16 | Agronomique Inst Nat Rech | Polymere phenolique a liaisons biaryles 5-5, procede pour sa preparation et utilisations |
| EP3071544B1 (en) | 2013-11-22 | 2022-07-06 | Polnox Corporation | Macromolecular antioxidants based on dual type moiety per molecule: structures methods of making and using the same |
| WO2018160879A2 (en) | 2017-03-01 | 2018-09-07 | Polnox Corporation | Macromolecular corrosion (mcin) inhibitors: structures, methods of making and using the same |
| WO2020262432A1 (ja) * | 2019-06-25 | 2020-12-30 | 株式会社Ｍｉｚｋａｎ Ｈｏｌｄｉｎｇｓ | 増粘剤、その製造方法、及びそれを含有する飲食品 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2545101B1 (fr) * | 1983-04-29 | 1985-08-16 | Agronomique Inst Nat Rech | Procede de modification des pectines de betterave, produits obtenus et leurs applications |
| US5346695A (en) * | 1991-03-27 | 1994-09-13 | Tampa Bay Research Institute | Methods of inhibiting HIV replication in vitro using polymers of p-hydroxylated cinnamic acids |
| GB2261671B (en) | 1991-11-16 | 1996-07-03 | Gb Biotech | Gel production from plant matter |
| RU2119758C1 (ru) | 1991-11-16 | 1998-10-10 | СПС Интернэшнл Инк. | Способ получения целлюлозосодержащего зернового экстракта |
| MX9207375A (es) * | 1991-12-18 | 1993-07-01 | Novo Nordisk As | Metodo para el curtido de cueros por medio de agentes de curtido. |
| BR9508350A (pt) | 1994-07-26 | 1997-11-04 | Novo Nordisk As | Processo para provocar a gelificação ou o aumento de viscosidade de um meio aquoso contento material polimérico propenso a gelificação produto geleficado produto de gel desidratado ou seco e uso dos produtos |
-
1995
- 1995-07-26 BR BR9508350A patent/BR9508350A/pt not_active IP Right Cessation
- 1995-07-26 AT AT95926378T patent/ATE198604T1/de not_active IP Right Cessation
- 1995-07-26 DE DE69519852T patent/DE69519852T2/de not_active Expired - Fee Related
- 1995-07-26 WO PCT/DK1995/000317 patent/WO1996003440A1/en active IP Right Grant
- 1995-07-26 ES ES95926378T patent/ES2155523T3/es not_active Expired - Lifetime
- 1995-07-26 AU AU30745/95A patent/AU3074595A/en not_active Abandoned
- 1995-07-26 EP EP95926378A patent/EP0750641B1/en not_active Expired - Lifetime
- 1995-07-26 HU HU9700237A patent/HU220197B/hu not_active IP Right Cessation
- 1995-07-26 US US08/732,260 patent/US6232101B1/en not_active Expired - Lifetime
- 1995-07-26 JP JP8505375A patent/JPH10502962A/ja not_active Ceased
- 1995-07-26 CZ CZ1997205A patent/CZ287861B6/cs not_active IP Right Cessation
- 1995-07-26 CA CA002195640A patent/CA2195640C/en not_active Expired - Fee Related
- 1995-07-26 PT PT95926378T patent/PT750641E/pt unknown
-
1997
- 1997-01-23 FI FI970274A patent/FI114987B/fi active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| CZ20597A3 (en) | 1997-05-14 |
| DE69519852T2 (de) | 2001-08-02 |
| PT750641E (pt) | 2001-06-29 |
| HU220197B (hu) | 2001-11-28 |
| FI970274A (fi) | 1997-01-23 |
| US6232101B1 (en) | 2001-05-15 |
| EP0750641B1 (en) | 2001-01-10 |
| ES2155523T3 (es) | 2001-05-16 |
| JPH10502962A (ja) | 1998-03-17 |
| AU3074595A (en) | 1996-02-22 |
| FI970274A0 (fi) | 1997-01-23 |
| BR9508350A (pt) | 1997-11-04 |
| CZ287861B6 (en) | 2001-02-14 |
| FI114987B (fi) | 2005-02-15 |
| WO1996003440A1 (en) | 1996-02-08 |
| DE69519852D1 (de) | 2001-02-15 |
| EP0750641A1 (en) | 1997-01-02 |
| HUT77999A (hu) | 1999-04-28 |
| CA2195640A1 (en) | 1996-02-08 |
| ATE198604T1 (de) | 2001-01-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed | ||
| MKLA | Lapsed |
Effective date: 20110726 |